


Femininity

by TeaRoses



Category: Pokemon
Genre: F/M
Language: English
Status: Completed
Published: 2010-02-27
Updated: 2010-02-27
Packaged: 2017-10-07 14:06:35
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,941
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/65873
Author URL: https://archiveofourown.org/users/TeaRoses/pseuds/TeaRoses
Summary: <blockquote class="userstuff">
              <p>Written in response to a request:  "James gives Ash crossdressing tips when Team Rocket ends up helping them get Pikachu back from Butch and Cassidy."  A little Rocketshipping (Jessie/James) and maybe some Pokeshipping (Ash/Misty) if you hold it sideways and squint at it.</p>
            </blockquote>





	Femininity

**Author's Note:**

> Thank you to little_details on LiveJournal for help with cross-dressing hints.
> 
> English names used. Mondo is a canon character from an untranslated CD-Drama.

Jessie and James were flopped exhausted against a tree in the Viridian forest when Misty came crashing through the brush.

"You two told me you were out of Team Rocket!" she shouted. "You said they even took Meowth away from you."

James opened an eye lazily. "We are. They fired us. See the lack of uniform?"

James was wearing denim jeans and a white shirt. Jessie had a white mini-dress.

"Then where's Pikachu?" demanded Misty.

Jessie snapped to attention at that point. "How should we know, brat?"

Misty sighed. "Ash is frantic."

Jessie rolled her eyes. "I have no idea. Since when were we capable of stealing anything for long, anyway?"

"Say Missy, I thought you were playing gym leader with your ditzy sisters," said James.

"That's Misty, and you know that. And I still am," said Misty. "I just took a break to camp out with Ash for a while. You know, for old times' sake."

"I'd think that kid would be the one thing on earth worse than your sisters," James replied.

"Who said you could insult my family?" challenged Misty.

James shrugged. "You want to insult mine? I'm running out of good ones."

"I have a few," said Jessie, putting her clenched fist on his shoulder.

"Look, it must have been Team Rocket!" insisted Misty.

"Did they leave a big red R at the scene?" asked Jessie.

"I think we're the only agents who would be stupid enough to do that," said James in a depressed voice.

Jessie nodded.

"I wonder if Mondo would know?" said James conversationally.

"Who's Mondo?" asked Misty in a slightly calmer tone.

"Our old assistant," said James. "He's still in the team. Administrative position."

"You guys had an assistant?" asked Misty. "I thought you were the failures of... well, you know…" she trailed off, mumbling.

James sighed. "You think we could make all that stuff ourselves? Mondo's a genius. If it weren't for him we would never have gotten a thing done. And before you say it, back before we met you kids there was a reason people were scared of us."

"If you say so," said Misty. "But could you really find out from this Mondo guy what happened? Won't he be worried about getting in trouble for telling?"

"Mondo just goes below people's radar most of the time. I doubt they'll even figure out it was him who told."

"Jessie has his cell phone number," said James. "That kid would do anything for her."

James suddenly spoke in a slightly different voice, a bit lower than his own, in a desperate eager tone. "Oh, sempai, you want my Ditto? Of course you will have my Ditto. You want a new jeep? My jeep is yours! You want me to take my shirt off and dance on the table? It shall be done!"

Jessie was laughing but shaking her head. "Mondo was loyal to both of us, James, and you know it. But I fail to see why we should bother him because of some twerp."

"What else have we got to do?"

Jessie shrugged and began dialing her cell phone. She did apparently reach Mondo, but had to reassure him several times that it was indeed her speaking. Then after a few pleas to him to slow down, she managed to ask some questions about Pikachu and apparently get a few answers. Finally she told him that James was well and closed the phone.

"It was Butch and Cassidy," she said in a musing tone.

"I thought the boss saved them for the really important projects," said James.

"We weren't one?" asked Misty.

"Pikachu was more our obsession," said James. "I think the boss let us do it to keep us out of the way, most of the time."

"I never did understand how the man ran a criminal organization with employees like us," sighed Jessie. "Anyway, apparently those two wanted to show us up, so they just marched right in with a new experimental tranquilizer and took the rat while you were sleeping. Mondo knows because they did call it in to the Boss, and he's sending someone to pick it up."

"If he were sending Mondo, we'd be in luck. But Mondo's supposed to be working on a new mecha, and whoever does go is supposed to be there tonight. We can't get your Pikachu back by then."

"Of course we can!" said Misty. "We have our Pokemon, and your Pokemon!"

"Who's we?" snapped Jessie. "Anyway, do you really think our pathetic team and whatever you have left can take on Butch and Cassidy? They have some major Pokemon now. Experimental ones the boss gave them. Plus real weapons. They're not like us."

Misty sat down, looking disgruntled. They all thought quietly for a few minutes.

Suddenly Misty looked up. "Hey, wait a minute. All Butch and Cassidy know is that somebody is picking up Pikachu. Anybody could show up, and they'd never suspect something was wrong."

James looked up. "Say, that's a point. We could disguise ourselves, and—"

Jessie interrupted. "Any moron can recognize you in your get-ups."

"We never did," said Misty.

Jessie said, "Hmmph," and they all went silent again.

"What about me?" asked Misty. "I could try to go in disguise. I've worn a Team Rocket uniform before!"

Jessie thought a moment. "They'd probably spot you. Besides I think the boss is sending one of his personal assistants; they wouldn't even wear uniforms."

"I bet they wouldn't recognize Ash in disguise," said Misty after a while. "Everyone knows him from his hat, and him carrying Pikachu around. Believe me, he looks totally different when he's not in those clothes."

"Well that's more information than I personally wanted to know," said James.

"That wasn't what I meant," snapped Misty. "Besides, he'll want to go himself. It's his Pikachu. Ash could say he's a new assistant."

"It still won't work," sighed Jessie. "The boss's personal assistants are all women. He's that kind of guy, if you get my drift. He gets new ones all the time, but Ash wouldn't be one."

James was laughing under his breath now. "What about Ashley?"

Misty look starry eyed for a moment, "That's a great idea!"

"What, dress the kid up like when we snuck him into Erika's gym? It'll never work. That was years ago, and even then it wouldn't have fooled those two," said Jessie.

"I don't know, they might spot him as a cross-dresser, but not as Ash Ketchum," insisted James.

"But if the boss hired any cross-dresser, he'd be a good one," insisted Jessie.

James opened his mouth and shut it again.

Misty said, "I still say it's worth a try, if you make him look really, really good. And I know you can!"

James looked proud. "I'll bet I could."

Jessie hesitated. "I don't know. I still want to know what's in it for us."

Misty thought. "I'll get you guys a decent Pokemon. If I can't get any gym leaders to cooperate I'll get you one of mine."

"Only one?" asked Jessie.

"You guys share everything, I thought," Misty replied.

James, "In the sense that she takes all my stuff, yes."

Misty sighed. "Two pokemon, then. Whatever it takes."

Jessie and James gave each other a look. Both nodded, and said in unison, "Get the kid."

Misty came back twenty minutes later trailing Ash.

"Are you guys sure about this?" he was asking.

"Kid got tall…" commented Jessie.

"He's still pretty skinny," said James. "We've got a chance."

"I'm scared," whimpered Ash.

"Don't worry so much, kid," said James. "The thing is, this time we can't just put you in a dress and slap a wig on. We've got to make this fool Butch and Cassidy."

Ash nodded. "If it will get Pikachu back, I guess I can trust you two one more time."

James nodded. "Have we ever steered you wrong? I mean, when we weren't trying to? I mean…"

"Shut up, James," said Jessie.

James went off into the trees and brought back a box. He began ruffling through it. "He's going to need a chest," he muttered.

"He's not wearing those inflatable things," warned Misty.

James snickered. "Those are only for me, kid…"

He pulled out a bag of rice. "Hey, I didn't know we had this, or we'd have eaten it ages ago. But it'll work."

"Work for what?" asked Misty.

"You put it in baggies, and stuff the baggies in a bra…"

Ash paled. "I have to wear a bra?"

"Don't go all wimpy on me now," said James, pulling out a bulky pair of underwear. "These should fit, and they'll give you some hips."

"I have hips."

James rolled his eyes. "Jessie, go and get some dresses for us to look through. I don't think any of mine are going to work with his coloring."

James got busy with the rice and a funnel. Jessie brought back a box, and James dug through it, finally coming up with a black and white piece of cloth.

"Go behind those trees and change, kid," he said to Ash, shoving various articles at him. Blushing, Ash complied.

"Is he going to have to tuck?" asked Jessie.

"Tuck what?" Misty asked.

Ash gave an incoherent shout from behind the trees.

"Never mind that, you'll be fine," said James dismissively.

Meanwhile Jessie had pulled a pair of high-heeled shoes and a wig out of another box.

She went behind the trees, producing another shout from Ash.

"Shut up, twerp, you don't have anything I haven't seen before."

Misty looked up. "That's more information than I really wanted."

James looked in another direction and hummed tunelessly.

More voices came from behind the trees.

"I can't walk in these!"

"Now you know how women feel!"

"I didn't want to know how women feel! Ouch!"

"Stop squirming, they're only bobby pins!"

Finally Jessie came out from behind the trees.

"He's ready," she said with a dramatic flourish.

Out from behind the trees walked... a woman. "She" wore a white dress with black swirls that showed off the curves of her figure. Long black hair framed "her" face.

Misty gasped. "Ash... I never thought you'd look this attractive as a woman."

"I never thought he'd look attractive at all," the former Team Rocket said in chorus.

Ash walked gingerly toward them in the high heels.

"Confidence, Ash," said James. "You're a Team Rocket agent making a pick-up."

Ash nodded. After fifteen minutes of walking practice, with Misty still staring, they proclaimed him ready.

"You'd better go alone, kid," said Jessie. "We'll only make some mistake if we follow you."

He nodded again and walked off through the trees. Misty watched after him.

"What do you think Butch and Cassidy will do to him if they figure out who he is?"

"Cassidy will be too jealous to notice," said Jessie waspishly. "I don't think Butch will hit on Ash though. He's too professional."

After hours of waiting and making up drastic scenarios, they heard approaching footsteps. Ash walked into the clearing triumphantly holding Pikachu. Everyone cheered.

"I guess you'd like to get out of those clothes now," said Jessie.

Ash blushed. "Not exactly. I'm kind of enjoying this. Anybody have a mirror? And hey, I didn't get to wear any make-up yet!"

Misty was still staring. "In make-up he really will look better than me."

Jessie went over to her. "You'll get used to it. Trust me."

"I will?"

"Sure. And say, have you ever thought of a tuxedo? I think it would be a nice look for you."

Misty agreed, and the sun set on the Viridian forest.


End file.
